2-Methyl-2-butene → 6-(3-Acetoxy-propoxy)-7-methoxy-1-(3-methoxy-benzoyl)-isoquinoline-4-carboxylic acid

Participants

Reaction Steps

To a stirred solution of afforded 6-(3-acetoxy-propoxy)-7-methoxy-1-(3-methoxy-benzoyl)-isoquinoline-4-carbaldehyde (20 mg, 0.045 mmol) in t-butanol (1 mL) and water (1 mL) solution was added sodium dihydrogenphosphate monohydrate (25.3 mg, 0.18 mmol), 2-methyl-2-butene (0.030 mL, 0.27 mmol) and sodium chlorite (24.8 mg, 0.27 mmol) at room temperature. The reaction suspension was then stirred at room temperature for 14 hrs. The resulting two-phase mixture was partitioned between dichloromethane and water and acidified to pH=3 by addition of acetic acid. The aqueous phase was then extracted with dichloromethane (3×20 mL). The combined extracts were washed with saturated aqueous sodium chloride solution (30 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford a brown semi-solid oil. The crude product was recrystallized in ethyl acetate and hexane to afford 6-(3-acetoxy-propoxy)-7-methoxy-1-(3-methoxy-benzoyl)-isoquinoline-4-carboxylic acid (8.0 mg, 39% yield) as a white solid: HR-MS m/e calcd for C24H23N1O8 (M−H+) 454.1496, found 454.1502; 1H NMR (300 MHz) compatible.

Provenance & Evidence